Rory's New Life
by PhillyWriter
Summary: Rory has entered in a new world at Chilton. And she realizes a new desire - a world where she has money and power, one that only her grandparents can provide for her.
1. Chapter 1

It had only been eight weeks. But that was all it took, eight Friday Night dinners, for Rory Gilmore to feel a pit in her stomach. All week long at Chilton she was surrounded by… them. The children of privilege. The children of wealth. They had fancy cars and lived in mansions. She lived in a small-town, miles away, in Stars Hollow. But her grandparents, whom she had only started to get to know… they had what she was drowning in.

It was hard for her, jumping feet first into her grandparents' world. She had barely known them. But now there she was every Friday, in her finest dress with a maid serving her a gourmet meal. Her grandfather expounding on his business as well as the Classics of education. Her grandmother talking about all the organizations she either ran directly or indirectly by her mastery of the rules of proper society. They treated her so well. Asking her about school. Encouraging her. Spoiling her, to her mom's chagrin, especially with a well-appointed bedroom in their house and a recent trip to a country club, which Rory enjoyed more than she let on.

This week had been particularly hard. The class work was piling up. Assignments in a struggling public school had been no problem for Rory. But at Chilton? She had to get caught up on a year's worth of Latin by the end of the semester. This was on top of having to sit by herself at lunch, looking at all of the cliques and their fiefdoms. To achieve her dreams, Rory knew she had to do more than just ace Latin. She had to find a way into the Chilton world and, not just that run it.

It was a Thursday afternoon and Rory went to her grandparents' house. They were expecting her as Rory called the night before in order to ask her grandfather for a book, Menken, followed by dinner.

Emily arrived to the front room as the maid opened the door. Gracious, smiling, beaming, still wearing the Chanel suit she bought for the day's D.A.R. meeting she chaired.

"Rory," Emily said. "It's no good to see you! Would you like a Diet Coke?"

Rory nodded and meekly said yes as Emily prepared the glass. With that, Richard stomped down the steps still clad in his bowtie from work.

"Rory, my dear," he said warmly, the book in his hand. "I found the original copy. It was just where I thought. I take it you'll be staying for dinner?"

Rory nodded. "Yes," she said. "But… But before that, there's something I'd like to say."

Emily and Richard both expressed concern.

"Are you okay" Emily asked.

"Oh, yes," Rory said as she took a seat on the sofa, with Richard and Emily across from her.

"Is it something at school?" Richard leaned forward.

"Oh, no," Rory said, taking a deep breath. "There's something I've been thinking about all week. Well, for a few weeks now. I… I just have to say it."

"What is it, dear," Emily asked.

Rory looked up at her grandparents.

"I want to live here. With you. Permanently."

Richard flinched, somewhat uncomfortably. He turned to Emily, who adjusted her posture upright, with a glint in her eye.

"And why is that, dear?" Emily said so gently. "And, Rory please sit up straight."

Rory nodded before mirroring her grandmother's rigid posture.

"Well, Grandma, Grandpa," Rory stammered a bit. "I… I didn't grow up with any of this. I didn't grow up with maids. I didn't grow up in a mansion."

"Oh, we certainly know that," Richard said.

"And… well… I don't understand why anyone would want to run away from this."

"And we certainly know that," Emily replied curtly.

"I mean the room you set up for me is bigger than the entire floor of our house," she said. "I know my mom hates this life. But… but I don't. I feel so comfortable here."

Emily placed her hands on the side of her chair, trying to hide the smirk from her face. Richard furrowed his brow curiously.

"And, well… I can also see it at school. The other students look down on me. They think I'm some country bumpkin. But they don't realize that I actually come from the same background as them. Heck… you have even more than more of my classmates' families."

Richard tried to swallow his chuckle.

"And I want to be the best. I have to be valedictorian to get into Harvard. I have to get involved in clubs. All of the applications look towards that," Rory said. "I can either schlep it back and forth to Mom's on a bus and have to deal with her making me watch bad movies and eat at Luke's… Or I can stay here and learn from you two. More than I have already."

Richard cast a side eye towards Emily. He wanted to thread this needle gingerly. But he knew his wife. She was not one to bite her tongue or jump at an opportunity.

"Well Rory," she said. "This is lovely to hear. Your mother always wanted to be independent and free. But if I'm hearing things correctly, Rory… It sounds like you want to be rich, successful and powerful."

The words flowed over Rory and sank in. A glow rushed upon her face and forced a smile upon her. It was something she never thought she wanted to aspire to. But now she realized the truth.

"Yes. I want to be rich, successful and powerful. Just like you and Grandpa."

Emily was now in a fully wide smile. Her daughter had so thoroughly rejected their world and their life, running off so young to live in a shed and act as a maid, taking their granddaughter away in the process. But now? Now their granddaughter was exposed to their world and was embracing it.

"What do you think, Richard?"

Richard took a deep breath. This conversation made him nervous. Rory was essentially a stranger to him just a few weeks ago. But since she was introduced to her life, he was smitten with his granddaughter. So smart and charming and brimming with unlimited potential. However, there were so many distractions in her life that, without a proper influence, could lead her astray. But at the same time, their daughter was back in their lives too.

"Well, Rory, this is a difficult position. I want more than anything to do what's best for you. But we have your mother to consider here. We know how awful it is to have your daughter gone from you."

Rory looked down and nodded.

"I know. This would devastate her."

"Yes, it would."

Emily pursed her lips and glared at her husband.

"Rory, dear. Would you mind going to your room? Your grandfather and I need to talk about this amongst ourselves before we find a solution."

Rory nodded and retreated. Both paused until she was out of earshot.

"Emily, if this girl moves in with us, we'll never see Lorelei again."

"Well, Richard, how long do you expect this to last with Lorelei to start with? She contacted us for us to pay for Rory's school. If she's able to afford it on her own somehow, she will rip this girl away from us," Emily snapped. "Heck, I might just breath too loudly and Lorelei might take her away. Away from Chilton. Away from us. Away from what she so clearly said she wants."

"I know, Emily," Richard said. "But still. You should know how much this will hurt Lorelei more than anymore."

Emily stared at the portrait of her, Richard and Lorelei.

"I do." She paused. "But, Richard, the reason why I insisted that Lorelei and Rory have dinner with us every Friday wasn't just to have Lorelei back in our lives. We know how hard-headed she is. But it was to have Rory. She needs to have proper influences in her life. She has our last name. I… We… wanted to show her the world that was at her fingertips. She wants it. And we can give it to her."

"But what about Lorelei? What about our daughter?"

Emily paused.

"Well, Richard," she said. "Lorelei ran away. Rory is running too us."

Richard side and shook his head. He was still apprehensive.

Rory did move to her room, but left the door open. She could not hear all of the words said, but she read the room. She turned her head and saw her grandfather's dark-oak toned study. Home to his books and work and the source of all he had accomplished. And she saw something truly important to him, above and bigger than the framed portrait of him with a younger Lorelei.

His diploma.

Rory felt another tinge and turned to the stairs.

"Grandma, Grandpa," Rory said. "I'm sorry to interrupt. But… there's something else I need to say."

"What's that, dear?"

"Well, Grandpa. I know you're apprehensive about this."

"Yes, Rory. I am."

"Well, as I said. I want to have what you and Grandma both have," Rory said. "And I know you two can shape me. But I know there's another place that can help me achieve all I'm capable of."

Rory paused and smiled.

"Yale."

Richard leaned back and slowly pulled off his glasses.

"Grandpa, if you let me live here… then I won't go to Harvard. I'll go to Yale instead. I'll be able to carry on the family name and tradition at the finest university in the world."

Emily, recognizing Rory understanding how to pull strings, beamed.

"Well, Richard."

A slow smile crept across Richard's face.

"You drive a hard bargain, Rory," he said. "Yes. If you want to go to Yale, I agree. Your grandmother and me will clearly give you the best opportunity to reach this goal."

He smiled and looked at Emily and then back at his granddaughter.

"Yes, Rory. You can live here."

Rory smiled so excitedly -

"BUT under certain conditions," he said. Rory sat back down, nodding.

"School has never been a problem with you. Nor shall it be. We expect nothing but top marks from you at all time, young lady."

"Of course, Grandpa."

"Yes. School will be your priority. And I know how much you enjoy reading. When you are done with your schoolwork, I will assign you some of my favorite texts. You will find a world of grand literature and words awaiting you," he boomed. "Heck, I believe by the time you enroll at Yale you'd be qualified to teach a course once you get through the reading list I'll craft for you."

"Of course, Grandpa. I'm already eyeing up all the books in your study. Like Menken."

"And, Rory," Emily said. "If you want to understand how to get your way and how to be in charge of others, well, dear, I'll arrange your schedule for you when you are finished with your schoolwork. There are so many galas and balls and events. I sure could use an assistant to help me make sure these events are perfect."

"Thank you, Grandma. I'm sure I'll learn from the best."

"Of course, we'll also make sure you shine at your own debutante ball."

Rory nodded. The picture of Lorelei in her dress always loomed over this room.

"But one more condition, Rory."

"Yes, Grandma."

"Your mother was quite difficult, as you know. I know teenage girls can be quite difficult. However, I will not have a repeat of her behavior," Emily said. "I will not tolerate any backtalk. If you grow frustrated with us at any time, just remember this was your idea. Everything you've ever wanted in the world is now your. But it can also be taken from you very, very quickly."

Rory paused. And took a deep breath.

"I understand," she said. "Don't worry, Grandma. I'll make your proud."

"I know you will, Rory," she said. "Richard, do you think some champagne is in order? After all, we should be celebrating Rory's… our… new life."

"Yes, I do," said Richard. "But, Rory, only one or two sips."

Emily yelled for Rosa, this week's maid. But before she could speak, Rory interjected.

"Rosa, we will need three glass of champagne," she barked. "And, also, make sure you are wearing white gloves when you serve our drinks. We don't want any of your fingerprints on our glassware."

Rosa quickly nodded before scurrying off. Richard looked at Rory askew while Emily smiled approvingly.

"I've wanted to be able to talk to a maid like that since my first dinner here," Rory said.

"You did a good job informing her of the details in life," Emily said.

Rosa came back in, wearing the gloves, as each grabbed a glass.

"To Rory," Richard said. "Our beloved granddaughter and a young woman the world awaits to conquer."

They sipped their champagne. Rory set her glass down.

"Grandma and Grandpa, may I be excused? I have some homework to do before dinner. And I guess I should call my mom."

There was a big pause.

"Yes, that," Richard said. "Let's take it slow. I don't believe your mother will be upset if you ask to spend the night here tonight, would she?"

"She does know you're staying for dinner, right?"

"Yes, she does," Rory said. "Yes. I think she'll believe that."

"Very good, Rory," Richard said, nodding, as his granddaughter ran off to her new bedroom.

They watched her disappear. Richard turned to his wife.

"I know you're worried about this, Richard," Emily said. "But it took me all of two months to sink my claws into Rory. Don't think I am ever, ever letting go. She belongs here, with us."

Richard's angst on the situation disappeared off his face as he sat back, kingly.

"She does," Richard said. "And we'll ensure that she's the better for it."


	2. Chapter 2

Rory woke up from bed. She wasn't sure if she was still sleeping. The bed she was in was a king sized bed, much larger than the twin that was largely on her messy bedroom floor. The room was covered in lace and pink and frills. She moved to the bathroom – her own – and saw it stocked with a variety of soaps and lotions. Her Chilton outfit was laid out and pressed perfectly, hanging, smelling new.

The surreal nature of her situation didn't change when she walked down the creaky steps into the kitchen. The first thing she noticed was the host of fruits and berries spread around a pyramid of muffins, bagels and a variety of jams. Rosa, the maid, scurried in with a plate of scrambled egg whites on a plate with whole wheat toast on the side. The maid then squeezed an orange to top off her juice, and placed a warm cup of French-pressed coffee in a porcelain mug on the table, too.

"How did you sleep last night, Rory?"

Emily's smile beamed across the kitchen table, with Richard next to her reading that morning's edition of the Financial Times. Rory's grandfather was already ready for work, his hair handsomely combed, bowtie straightened. Emily was already looking old-money perfect – hair parted with a red and blue checkered designer top paired marvelously with a black skirt.

Rory sat down and the reality of the situation washed over her. She had thought for some time, weeks, about what it would be like not just coming over to her grandparents' estate for dinner, but to actually live there. And it was waking up to the smell of breads with a cup of gourmet coffee prepared and her school outfit not in a pile on the floor. And she smiled as she sat down.

"It was perfect," Rory said as her grandmother's smile somehow grew even larger.

Rory started to eat her breakfast.

"Well, there's no need to beat around the bush, Rory," Emily said. "Dinner's tonight and we have to figure out a way to tell your mother about what it is you want."

Rory just stared down.

"Grandma, I don't know –"

Emily's eyes narrowed. She was afraid of this.

"No, Grandma, don't worry. I want to live here." Emily relaxed back. "But… I don't know if tonight's the night. This is just so fast. I don't know if I'm ready yet.

"You're not," Richard said, folding his newspaper down. "You're not ready yet. And, Emily, we're not either."

Emily's glare narrowed at her husband's.

"I sat up last night thinking about this situation. And this is a tough situation for you. And it is for us, too," Richard said. "So I have decided that this is something we need to ease into." 

Emily obviously did not like Richard's decision and, most importantly, not included in the process. But Rory was obviously more relaxed.

"Rory, you will stay the weekend," Richard said. "And it will be the type of weekend we envision for you. But we have your mother to consider in this, too."

Rory nodded.

"Well, Grandpa, she has a very busy weekend," Rory said. "There's a huge wedding at the Inn. The ceremony is Sunday night—"

"Who gets married on a Sunday night," Emily asked.

"So, I was essentially going to be on my own this weekend. I was supposed to meet Lane. And I have the movies and books and could always go to the Inn," Rory said. "But this is a really busy weekend for Mom."

"Excellent," Emily said. "So then your stay shouldn't upset her."

"No," Rory said. "I really do have a huge study meeting with Paris after school today. And it actually does make sense for me to come right after school."

"How is the Chilton golf team going, Rory," Richard asked.

"Well, Grandpa, I do have to go to one more round for it to count as my athletic credit," Rory said.

"Wonderful. I'll arrange for us to have a tee time at the club tomorrow morning,' Richard said. "You can tell your mother that it will just be easier for you to stay here as opposed to her having to drive."

"And, Richard, I'm sure you'll inquire about membership," Emily asked. 

"Of course. If it's what Rory wants.'

Rory smiled as her grandparents looked at her.

"Yes," she said. "It's what I want."

Rory took a big sip of her coffee.

"Maybe I should also tell mom I have a big science lab to do, so I have to go back to Chilton," Rory said. Emily's lips moved together. She enjoyed seeing her granddaughter think about ways to scheme.

"Wonderful, Rory," Emily said. "I assume this is a bit of a… well… exaggeration?"

Rory flashed a conspirator's smile at her grandmother with a bite of a bagel in her mouth.

"Good. Because I have so many ideas for outfits for you already. I've just been dreaming of seeing you in Valentino dresses. And, of course, some Tiffany earrings. And afterwards is a big meeting of the Mark Twain Society. The women there will just absolutely adore you."

Richard stood up.

"And I will drop you home Sunday night," Richard said. "No ifs, ands or butts. I'll get the car ready, Rory."

He put his newspaper down and went to the other room.

"I know telling that mother of yours anything will be difficult. She's always been so emotional," Emily said. "But trust me. If this is what you want, then this is what you'll have."

Rory smiled and stood up.

"What I would really like most is my coffee for school," Rory said with a tone of newfound authority in her voice as Rosa scurried with a hot thermos. Rory snatched it.

"Thank you, Grandma."

And off she went to Chilton. Not on an hour-long bus ride where she had to walk past classmates being dropped off in luxury cars. But dropped off by her wealthy grandfather in his Jaguar.


	3. Chapter 3

The bell rang. Lorelei walked in as the maid answered, wearing a black dress with a spaghetti sleeves.

"Ah, Lorelei. The daughter who things 6:00 is actually closer to 7," Emily said with her customary sarcastic tone.

"I'm sorry, Mom," Lorelei said, with her customary exasperation. "This family at the Inn this weekend is driving us crazy. And then I hit some traffic near Waterbury."

"Who goes to Waterbury," Emily asked. "Is there anything even there anymore? Besides drugs?"

"Yes, Mom," Lorelei said. "It's all drugs. One big city on drugs."

Emily scoffed at Lorelei as she prepared her drink. Just then, Richard entered the room, with another financial newspaper in his hand.

"Lorelei," he bellowed, trying to hide his nervousness as his family's dynamic had changed so drastically without his daughter's knowledge.

"Hello, Dad," Lorelei said. "So, uhm, where is she? You know. What's her name. My daughter. I can't remember her name."

Emily shook her head disdainfully.

"Rory," she yelled. "Your mother's here."

Rory had been dreading this. She had been in her room studying for the past 90 minutes. Her grandmother had purchased for her a dress for the evening – a purple number with a designer with a hard-to-pronounce last name. She put the books down and walked down the steps.

"Hi, Mom," she said sheepishly.

"Why don't you look nice," Lorelei said before turning to Emily. "In an outfit I don't remember buying for you."

"What, am I supposed to let the girl just wear her school outfit all day?"

"Well, Rory has her own clothes at home. And that's why I like you coming home. So you can wear your own clothes and my mother doesn't have to buy you something that costs as much as the mortgage," Lorelei said.

"I know, Mom. I'm sorry. It's just that I have such a big test coming up and you're so busy with this wedding. It made such sense to just come right here. And Grandma…" 

Lorelei looked at her mom.

"Yes. I know what your grandmother is like."

Emily just shooed Lorelei away before they headed to dinner.

The meal was the typical fancy affair – some sort of rare bird with fresh vegetables. The Gilmores made their usual talk – Lorelei complaining about this wedding ("Who gets married on a Sunday?" she said) with Rory talking about Chilton and Emily talking about DAR affairs. Richard stayed silent the whole time. This wasn't unusual for him, but his tense nature was clear to Rory, who was the reason why he was so tense.

Finally, as dinner wore down, Rory spoke up.

"So, Mom. I have a question for you."

"Yessssss. Let me guess. You want to know if you can take my Sonny and Cher records. The answer is no. You can't."

"Oh, no. So I found out today that I have to go to one more Chilton golf team outing to get my credit for athletics," Rory said.

Lorelei pointed. "Wah ha!" she said in her best Ralph Wiggums voice.

"I know, I know."

"Rory told me this when she arrived," Richard said. "And I took the liberty of arranging a golf lesson for her at the club. However, the only time I could get was at 7 AM."

"7."

"Yes. 7."

"As in the 7 that comes after 6? And before 8?"

"Yes. That's what time the lesson was available."

"For all the years you have been going to this club, you couldn't have gotten a practice time at something a little bit earlier? Because I am going to have to wake up so early to get her here."

"Well Mom. That's what I wanted to ask. I know how busy you are. So could I just stay here tonight? It would be so much easier… for you. And then I'll be able to go right back to school."

"School? What about Lane? And the Inn? That's, like the only time I can see you this weekend."

"I know, Mom. But this science lab it's so crazy."

"And so is this wedding. We have to release 200 ceremonial birds upon nightfall. These people," Lorelei said.

"So, Lorelei, with this bird wrangling and your daughter's science lab, why can't she stay here tomorrow night as well?"

"Are you sure? Don't you have some, like, galas to attend and people to boss around?"

Emily shook her head.

"Well, it sure beats having to corral birds for strangers," Emily said. "No. It's not a problem. Rory is always welcome here. Anytime she wants."

Rory flashed a nervous smile at her grandmother, who flexed her eyebrows as she sipped water.

"I'll take her home Sunday, Lorelei," Richard explained. "I will save you the trip since you seem so busy."

"Seem is not the word," Lorelei said. "And, with that, I have to get back. Tonight the bride and groom want all of their guests to reenact their favorite songs from Grease 2."

"That musical with the street people," Emily asked.

"No. The sequel to that."

"They made a sequel to Grease?"

"Yes."

"Why?"

"I don't know. No one knows. But, alas, I have to go." Lorelei stood up.

Rory stood up, too. And her mom embraced her with a hug.

"This is the longest we'll ever be apart," Lorelei said in a parody of a dramatic voice.

"Oh, you'll get over it," Rory said.

The door shut. Rory looked down as her grandparents moved to the living room. 

"Now, Rory. What are you upset about?" Emily said a bit sharply. "This is, after all, what you want."

"No, you're right, Grandma. It is," Rory said. "It's just that I've never lied to my mom before. It's… I don't know. I don't like it." 

Richard stood up to prepare himself a drink.

"You did not lie, Rory," Emily said. "You just… fibbed a little bit." 

"Rory, you will feel guilty about this," Richard said. "In fact, you SHOULD feel guilty."

Emily glared at Richard angrily. The last thing she wanted was for Rory to feel bad.

"But what you did tonight was the first step in learning how the world works. Do you think I just got to where I am in the insurance world by playing fair?" He sipped his scotch.

"There are plenty of people like me who come from fine backgrounds and fine colleges who are industrious and hard working. But to get to where you want to go. To get to where you deserve, sometimes you have to fight a little dirty." 

Rory looked up as she stood behind a chair.

"I've had to do some things over the years to move people aside and step over them," Richard said. "It's the nature of the world. No one likes to admit this but it's a fact. You'll have to do it when you start working. Heck, you've probably should be doing this at Chilton already. And if you're able to learn this young by playing your mother like this now… then you'll be able to do whatever it takes to get ahead of people you don't care about."

Rory took a deep breath.

"Rory," Emily said. "It's your mother. She ran away from here pregnant at the age of 16. She ran away from the life we gave her. But I never, not once, stopped loving her. And she'll never stop loving you."

Emily stood and put her arm around Rory.

"She did what was she thought was best. It ripped our heart out, but that was the choice she made. And you're making the same choice for you," Emily said. "And it's the right choice if you want this life."

Rory looked up at both her grandparents.

"This is the life I want," she said. "This is the life I deserve."

Richard and Emily smiled.

"Very good, Rory," Emily said. "You handled yourself fantastically."

"Now, Rory," Richard said. "I've set up a Victrola in your room. And in my study is a record - excerpts from Puccini's opera La Boehme. It's my favorite piece of his. I've set that aside for you, as well as a copy of the best biography written about him. I'd like for you to listen to the opera and read the biography. And then, at 9, we'll discuss what you've learned en route to your golf lesson."

"9? I thought you said 7?"

Richard smiled.

"Like I said, Rory," Richard laughed. "Sometimes you have to say some things to get what you want. And I want you here."

Rory gave each one of her grandparents a hug before jutting off to her room.

Richard smiled as she went up the steps. Out of view, he turned to his wife.

"Emily, I am nervous about this," he said.

"What? About Lorelei? We discussed this already. She's been mad at us her whole life," Emily said.

"No. I'm nervous about Rory," Richard said. "She wants this now. But teenagers are fickle. She could change her mind at any second."

Emily poured a drink and leaned back in the chair.

"Richard, Lorelei was rebellious and wanted to be oh-so independent," Emily said. "She raised Rory not as a parent but as a peer. Rory's not Lorelei. She doesn't want to be independent. She wants to be in charge. She has social ambition."

Emily smirked.

"But she's rebelling against Lorelei by not being rebellious at all," Emily said, pleased. "I could tell from the very first dinner that girl's biggest joy in life comes with a desire to please. But she's learning she doesn't have to please everyone. Just a select few. And, Richard. We're that select few."

"I hope so, my dear," Richard said. "I hope so."


End file.
